Liam Payne tragically died on October 16, 2024 after falling from his third floor hotel room in Buenos Aires, Argentina.

The former One Direction band member had been enjoying a romantic vacation with girlfriend Kate Cassidy shortly before his sudden death.

Payne was also reportedly struggling with legal issues related to his ex, Maya Henry, in the days leading up to his death.

The British-born musician, who shared a young son named Bear with his ex-partner Cheryl Cole, has a complicated relationship list.

Read on to look back at Payne's dating history:

Danielle Peazer

Payne and Danielle Peazer began dating in 2010 – the same year his pop band was formed with Niall Horan, Harry Styles, Zayn Malik and Louis Tomlinson.

They met off and on, broke up briefly and got back together in 2012.

Their relationship appeared to be on the rocks in early 2013 – but they still surprised fans nearly nine years after their split when they were spotted leaving a party together in June 2022.

Despite the public appearance, nothing seemed to happen between the former flames.

Sophia Smith

The “X Factor” alum began dating his childhood friend Sophia Smith in May 2013.

They confirmed their split two years later, with Payne admitting he was heartbroken.

“I'm absolutely devastated to have split up with Sophia,” he told The Sun at the time (via J14 Magazine). “Being on the tour all year and being away from it was so hard. We spent so much time apart. But to please someone, sometimes it is better not to do what your heart desires, but to do what is better for you.”

Cheryl Cole

The late singer and Cheryl Cole began dating in February 2016 – six years after she judged him as a contestant on The X Factor.

At the time, Cole had just separated from her ex-husband, French restaurateur Jean-Bernard Fernandez-Versini, whom she married in 2014 after three months of dating.

In March 2017, Payne and Cole welcomed their first child, a son named Bear. However: A year later, the couple announced that they were ending their relationship.

“Cheryl and I are sad to announce that we are going our separate ways,” Payne wrote on X on July 1, 2018. “It was a difficult decision for us.”

“We still have so much love for each other as a family,” he continued. “Bear is our world and we ask that you respect his privacy as we navigate this situation together.”

Naomi Campbell

Payne and Naomi Campbell, who was 23 years older than the singer, sparked romance rumors in January 2019.

At the time, they were caught exchanging flirtatious messages on social media – leading fans to believe they were more than just friends.

“Perfection in a human…don't give me those eyes,” Payne commented on one of the model's posts, while Campbell called the singer a “beautiful soul” in the comments section of his January 15, 2019 photo.

Maya Henry

Maya Henry and Payne got together in 2018 following his split from Cole.

He and the model dated for two years before getting engaged, and Payne gave her an engagement ring estimated to be worth more than $4 million.

Unfortunately, their engagement didn't last long and they broke up ten months later amid rumors that he had cheated on her.

Henry reappeared in Payne's life shortly before his death, with an insider claiming in October 2024 that he was “extremely overwhelmed by all the legal issues” after being issued a cease-and-desist letter by his ex's lawyers.

He allegedly received the letter “after new and worrying information emerged,” the Daily Mail reported.

Just days before his death, Henry eerily discussed how Payne often predicted his death in order to manipulate her.

Aliana Mawla

Payne was recovering from his split from Henry and Aliana Mawla in May 2022.

Rumors circulated at the time that Mawla was the woman Payne allegedly cheated with while he was engaged to Henry – although the internet personality denied those claims.

“Under no circumstances would Aliana have engaged in a public relationship as such if the comments made were true,” Mawla's rep told E! News back then.

The couple did not survive the scandal and in the end they went their separate ways.

Kate Cassidy

Kate Cassidy and Payne began seeing each other in October 2022, shortly after he and Mawla's relationship hit rock bottom.

They confirmed their relationship by walking the British Fashion Awards red carpet together this year and went Instagram official in January 2023.

The lovebirds were rocked by breakup rumors in May this year – but they put an end to the talk when they showed up at a party together the following month.

Afterwards, Payne and Cassidy seemed inseparable and attended major life events together.

The couple flew to Argentina together to attend Niall Horan's concert in Buenos Aires on October 2, 2024.

Cassidy left the country alone on October 14 – just two days before Payne later fell to his death from an Argentine hotel.